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Alkaloids and coumarins from Zanthoxylum flavum: Dihydrorutaecarpine, a novel β-indoloquinazoline alkaloid
Short Reports
578
neutml and acidic fraction and the basic CT-ICI,-soluble Fraction separated into individual constituents bj a corn-bination of column chromatography with benzene. henzene-EtOAc, CHCI:, and CHCI,-MeOH. Elution with CHCIs afforded a compound ‘-1.48mg (0~0006”~root, fresh wt. not present in the aerial parts) mp 20@201” from EtQH (lit. [2] 196-198” from CHClsMeOH), M+ na/e 367, 111 (CZoHr,NOs, found 367, 106) UV &,&EtOH) (log E): 207 nm (4.56), 239 (4.461, 290 (4*38), 317 (4.35), UV &,,,(EtQH + 1N HCI). 245 nm, 2975,337, 380 (Sh). IR (KBr)vmsxcm-l, 2945, 2880, 1685, 1625, 1590. NMR (CDCls, 6 ppm) 2.39 (3H, S, N-Me), 250-350 (4H, m, -CH2-CHz-), 4.76,5*16 (2H, each ABq, I 16 Hz, Ar--CH2-0), 5.85 (2H, s, O-CH#), 6.08 (2H, s, O-CH,-Q), 650, 660 (each lH, s, aromatic proton), 6.83 (lH, d, J 8 Hz, aromatic proton) and 7.76 (HZ, d, J 8 Hz, aromatic proton). Mass fragmentation: M’ m/e 367 (7%). 352 (5%), 205 (5?,), 190 (X50/,;),188 (77%), 178 (86x), 162 (78:/,), 151 (locr,‘b). R,. 052 fC,H,EtOAc = 2: l), 0.73 (CHCl,-MeOH = 20: 1) on silica gel H. These physical data showed A was identical with the isoqu~ol~e alkaloid corydali~~rone* [2] and was confirmed by its identity with an authentic sample. This alkaloid has been previously reported only from Cory d&i intim. Elutiou with benzene afforded pale yellow crystals, B, (aerial part 1.5 mg 000018% of fr. wt. root 15 mg O+)OlS%of fr. wt.) mp 278-280” (decomp. from CHCI,EtOH), M+ m/e 317, 067 (C19H1104N found 317, 069), UV /Z,,,(EtOH) nm 215,244,282,296,329, IR (KBr)v,,, 2890,1640,1590,1500, 1450, NMR (CFsCOOD, S ppm), 6.22, 6.49 (2H, each s, Q-CH,--0), 7.41, ‘7.94 (lH, each s), 7.92 and 844 (lH, each d, J 8 Hz), 8.14 and 844 (lH, each d, J 8 Hz) and 9.50 (lH, d, J 8 Hz). Mass fragmentation; M+ 317 (lOO’$&259 (7.1%) 202 (11.5x), 174 (53”,), 158 (11~5%).These physical data for B agreed with those of authentic nor~nguina~ne isolated from the callus [3], and this base was identified by comparison with an authentic sample. Later this base has been isolated from a papaveraceous plant. Argemone albifora c41. Elution with CHCls afforded plates, C, 4.5 mg (@O&X4%fr. wt aerial part, not identified in root) mp 184-185-5” (from EtOH}, NMR spectrum (CDCI,, 6 ppm), 254 (3H, s, N-Me), 3.70 (3H s, OMe), 3.92 (6H, s, OMe), 6.70 (lH, s, aromatic), 684 (2H, s, aromatic) and 8.80 (lH, s, OH, disappeared after DzO exchange), * Corydalispirone was reported recently by G. Nonaka and I. Nisbioka [2].
Phyiochemistry,
these values were ahost same with authentic isocorydine. [SJ. Mass fragmentation M’ 341 (WA), 326 (M” -15, looo/,), 310 (M’ -31, 49x), 298 (M+ -43, 4+47{)were identical with those of an authentic sample. The CHCls-MeOH fraction was purified by preparative TLC (Si gel, benzeneMeOH = 3:2), followed by recrystallization from EtOH affording colorless prisms, L?, mp 166-168” (macro) (172-173” micro, lit. [6] 169-171”). A mixed melting point with an authentic sample of kallocryptopine mp 155-157” (macro) (161-163” micro) gave 164-166” (macro). The IR absorption spectrum of the base f), showed some minor digerences to that of a-allocryptopine in KBr preparation, but gave identical spectra in CHCl,. The NMR and mass fra~entation pattern were identical with u-alfocryptopine, on the basis of the above results therefore L) may be the so-called fi-allocryptopine [6]. In addition, protopine, cc-alfocryptopine, dihydrosanguinarine, ~ngui~rin~ oxy~~arine and chelerythrine, and megnoflorine (from the quaternary base fraction) were identified by direct comparison (NMR, MS, TLC etc.) with authentic samples in a similar manner as reported previously [3,73. These alkaloids were identified in both parts of the plant. The isolation and identification of all these ,alkaloids, except protopine and a-akcryptopine are first report from this species. ~~~ow~d~e~nrs-.We thank Prof T. Furuya, Kitaaato University for kind encauragement, Prof I. Nisbioka and Dr. 0. Nom&a, Kyushu University, Prof II. Ishii, Chiba University, Dr. S. Naruto, Research Laboratories, Dainiuuon Pharmaceutical Co., Ltd. for kind supply of &mples.*ihanks are also due to the members of Central Analytical Laboratory of this University for NMR and MS measurements.
REFBXRENCE§ 1. Kojima, K. and Anda Y. (1951) f. Pkurm. Sot. Jup. 71, 625. 2. Nonaka, G. and Nishioka. 1. (197.5) Chem Pharm. Buk
23,284:
3. Furuya, T., Ikuta, A. and Syono, K. (1972) Phytochemistry 11, 304j. 4. Haisova, K., Slav& I. and Dolejs, It. (1973) C&l. Czech. Chem. Commun. 38, 3312. 5. Edwards,‘0 E. and flanda, K. L. (l%l) Can. .I. Chem, 39, rsot. 6. Seine, T. 0. and Willette, R. E. (1960) J. Am. Pharm. Assoc. 49, 368. 7. Ikuta, A., Syono, K. and Furuya, T. (1974) Phyt~rn~s~y
13, 2175.
1974 Vol. 15, pp 578-579. Pergamon
Press Prloted zn England
ALKALOIDS AND COUMARINS FROM ZANTHOX YLUM FLA VUM : DIHY~ROR~AECARF~E. A NOVEL P-INDOLOQUINAZOLINE ALKALOID* PETERG. WATERMAN. Department of Pharmaceutical
Chemistry, University of Strathclyde, Glasgow Gl IXW, Scotland (Receiwd 26 September 1975)
Key Wotd Mex-Zanthux~turn thin-bone; ~~ophenanthrid~e;
&rum; Rutaceae; alkaloids; fl~indoloquinuolinr. dihydrorutse~arpmc. canchelery~rine; nitidine; fur~~~~um~rln. imper;ltorrn. ~hzm,xaxanom~.
Pl~plr. Zu~t~xyi~ ~#~ Vahl. (syn. Fwum $auu Krug. et Urb.) Cl]. Voucher. Jimenez 5980 has been de
posited at the herbarium of the Royal Botanic Garden, Edinburgh. Source. Hill sides above La Cue&a, Santiago
519
Short Reports
Province, Dominican Republic. Uses. The wood, known commercially as Jamaican Satinwood, is a timber of high quality [2]. Previous work. The coumarins xanthotoxin, psoralen and suberosin [3] and uncharacterised alkaloids [4] from the wood. PIant parts examined. Root and stem barks. Present work. Soxhlet extraction of the stem bark (200g) with petrol @O-6@), concn of the extract and column chromatography ever Al,O,, eluting with EtOAc, gave imperatorin (75mg) mp 101” (lit. [S] 102-103”). Found M+ 270.0899, C1&11404 requires 270.0892. UV, IR, MS, PMR, were all in close agreement with published data [5-73. No other compounds were isolated from petrol or MeOH extracts of the stem bark but traces of alkaloid were detected. The root bark (1OOg) was similarly extracted with petrol, then CHC&, then MeOH. On shaking with 1N HCl the concn. petrol extract gave a yellow ppt. of chelerythrine chloride (14 mg) mp 200”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Badcation of the acid layer with NI&OH and reextraction into CH,Cl, gave canthin&one (6mg) mp 165”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Similar treatment of the CHCIJ extract gave, on addition of HCl, a yellow-green ppt. of nitidine chloride (46mg) mp 220”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Re-examination of the original petrol extract from the root bark revealed the presence of a further alkaloid which was purified by column chromatography over Si gel, eluting with CHCl,, to give white needles (13 mg) mp 168”. [a]$’ -21 (CHCl,; c 0.1). Found M+ 289.1218, C,,H,,N,O requires 289.1215. UV lgAzWnm (log E): 275(3.89), 292(3.76), 304sla(3.45), 31q3.24). IR v,,, (KCl) cn- ‘: 3350-3320 (NH), 1680 (CO), 1610, 1470, 1375. PMR @MHz, CDQ): 6 3.28 (2H, t, J 7Hz, CH,-14), 4.30 @I-I, t, J 7Hz, C&-15), 690 (lH, d, J 2Hz, H-6), 7.3g8.60 (8H, m, 8 x H-Ar), >lOOO (2H, both replaceable by DzO, 2 x N-H). MS: m/e 289(14%), 288(2), 287(06), 170(0.4), 169(1.0), 159(1.5), 147(3.3), 146(1.4), 143(100), 142(8.3), 130(33), 119(@4), 115(5.6). The occurrence of 3 x N in the molecule suggested the alkaloid was of the rare fl-indoloquinazoline class IUIOWII only from the Rutaceae [8]. This assumption was sustained by examination of IR (CO and NH) and MS. The complex fragmentation pattern of the latter can be rational&d by postulating fission of the b-indoloquinazoline nucleus between C6-N, and C12-N13 or between C,;C, and either N,&, or C14-C1s. The occurrence of the indolic fragments at m/e 143 and m/e 130 as major ions is in accord with findings for similar compounds [9,10]. The PMR confirmed both the presence of the 3 C-CH,-CHIN< moiety[l l] and the lack of any substitution on the molecule. The combined spectral data thus suggested that this was a novel member of the 8indoloquinazoline class of alkaloids in which the empirical formula C,sH,,NJO had been previously unknown. From the lack of substituents, presence of 2 x NH, optical activity and UV, in which 1,,is in close agreement with evodiamine (l), it seems that this new alkaloid must be dihydrorutaecarpine (2).
* Part 7 in the series “Chemosystematics For Part 6 see ref. [S].
in the Rutaceae”.
( 1) R = Me
(2) R = H
Direct evidence for structure (2) was obtained by reduction with LiAlH4 in dry Et,0 [1x13]. Refluxing for 10 hr gave, on recrystallisation from EtOH, indolo-[2’,3’ :3,4]-pyrido-2, lb-quinazoline, mp 162” (lit. [12] 161-163”), identical in all respects (UV, IR, mmp) with material obtained on reduction of rutaecarpine by the same method. Further evidence for structure (2) was obtained from methylation with Me1 in boiling MeOH. A mixture was obtained the major component of which was identical (TLC-3 systems) with evodiamine. Examination of the partially purified MeOH extract of the root bark by methods previously described [14] revealed the presence of small amounts of quaternary alkaloids of which one was tembetarine (TLC, UV). Biological signijcance. Whilst the type and distribution of alkaloids in 2. flauum appears typical of the genus [8,15] the presence of canthin-6-one and dihydrorutaecarpine may have additional systematic significance. Certainly the recent suggestion [16] that a close biochemical relationship exists between Central American and South East Asian species is supported by the isolation of a /?-indoloquinazoline from Z. jautun. Acknowledgemenr~The author wishes to extend his thanks to Dr. J. Jimenez, Calle Maxim0 Gomez 34, Santiago de 10s Caballeros, Dominican Republic, for the collection and identification of plant material and to Dr. R. D. Waigh, Department of Pharmaceutical Chemistry, University of Strathclyde, for PMR spectra. REFERENCES
1. Wilson, P. (1911) North Atnerican Florq Vol. 25, p. 196; Adams, C. D. (1972) Flowering Plants of Jamaica, p. 385, University of the West Indies, Mona, Jamaica. 2. Department of Scientific and Industrial Research, London (19561 Handbook of Hardwoods. D. 209. H.M.S.O. 3. King, J. E., Housliy, J. R. and i
578
neutml and acidic fraction and the basic CT-ICI,-soluble Fraction separated into individual constituents bj a corn-bination of column chromatography with benzene. henzene-EtOAc, CHCI:, and CHCI,-MeOH. Elution with CHCIs afforded a compound ‘-1.48mg (0~0006”~root, fresh wt. not present in the aerial parts) mp 20@201” from EtQH (lit. [2] 196-198” from CHClsMeOH), M+ na/e 367, 111 (CZoHr,NOs, found 367, 106) UV &,&EtOH) (log E): 207 nm (4.56), 239 (4.461, 290 (4*38), 317 (4.35), UV &,,,(EtQH + 1N HCI). 245 nm, 2975,337, 380 (Sh). IR (KBr)vmsxcm-l, 2945, 2880, 1685, 1625, 1590. NMR (CDCls, 6 ppm) 2.39 (3H, S, N-Me), 250-350 (4H, m, -CH2-CHz-), 4.76,5*16 (2H, each ABq, I 16 Hz, Ar--CH2-0), 5.85 (2H, s, O-CH#), 6.08 (2H, s, O-CH,-Q), 650, 660 (each lH, s, aromatic proton), 6.83 (lH, d, J 8 Hz, aromatic proton) and 7.76 (HZ, d, J 8 Hz, aromatic proton). Mass fragmentation: M’ m/e 367 (7%). 352 (5%), 205 (5?,), 190 (X50/,;),188 (77%), 178 (86x), 162 (78:/,), 151 (locr,‘b). R,. 052 fC,H,EtOAc = 2: l), 0.73 (CHCl,-MeOH = 20: 1) on silica gel H. These physical data showed A was identical with the isoqu~ol~e alkaloid corydali~~rone* [2] and was confirmed by its identity with an authentic sample. This alkaloid has been previously reported only from Cory d&i intim. Elutiou with benzene afforded pale yellow crystals, B, (aerial part 1.5 mg 000018% of fr. wt. root 15 mg O+)OlS%of fr. wt.) mp 278-280” (decomp. from CHCI,EtOH), M+ m/e 317, 067 (C19H1104N found 317, 069), UV /Z,,,(EtOH) nm 215,244,282,296,329, IR (KBr)v,,, 2890,1640,1590,1500, 1450, NMR (CFsCOOD, S ppm), 6.22, 6.49 (2H, each s, Q-CH,--0), 7.41, ‘7.94 (lH, each s), 7.92 and 844 (lH, each d, J 8 Hz), 8.14 and 844 (lH, each d, J 8 Hz) and 9.50 (lH, d, J 8 Hz). Mass fragmentation; M+ 317 (lOO’$&259 (7.1%) 202 (11.5x), 174 (53”,), 158 (11~5%).These physical data for B agreed with those of authentic nor~nguina~ne isolated from the callus [3], and this base was identified by comparison with an authentic sample. Later this base has been isolated from a papaveraceous plant. Argemone albifora c41. Elution with CHCls afforded plates, C, 4.5 mg (@O&X4%fr. wt aerial part, not identified in root) mp 184-185-5” (from EtOH}, NMR spectrum (CDCI,, 6 ppm), 254 (3H, s, N-Me), 3.70 (3H s, OMe), 3.92 (6H, s, OMe), 6.70 (lH, s, aromatic), 684 (2H, s, aromatic) and 8.80 (lH, s, OH, disappeared after DzO exchange), * Corydalispirone was reported recently by G. Nonaka and I. Nisbioka [2].
Phyiochemistry,
these values were ahost same with authentic isocorydine. [SJ. Mass fragmentation M’ 341 (WA), 326 (M” -15, looo/,), 310 (M’ -31, 49x), 298 (M+ -43, 4+47{)were identical with those of an authentic sample. The CHCls-MeOH fraction was purified by preparative TLC (Si gel, benzeneMeOH = 3:2), followed by recrystallization from EtOH affording colorless prisms, L?, mp 166-168” (macro) (172-173” micro, lit. [6] 169-171”). A mixed melting point with an authentic sample of kallocryptopine mp 155-157” (macro) (161-163” micro) gave 164-166” (macro). The IR absorption spectrum of the base f), showed some minor digerences to that of a-allocryptopine in KBr preparation, but gave identical spectra in CHCl,. The NMR and mass fra~entation pattern were identical with u-alfocryptopine, on the basis of the above results therefore L) may be the so-called fi-allocryptopine [6]. In addition, protopine, cc-alfocryptopine, dihydrosanguinarine, ~ngui~rin~ oxy~~arine and chelerythrine, and megnoflorine (from the quaternary base fraction) were identified by direct comparison (NMR, MS, TLC etc.) with authentic samples in a similar manner as reported previously [3,73. These alkaloids were identified in both parts of the plant. The isolation and identification of all these ,alkaloids, except protopine and a-akcryptopine are first report from this species. ~~~ow~d~e~nrs-.We thank Prof T. Furuya, Kitaaato University for kind encauragement, Prof I. Nisbioka and Dr. 0. Nom&a, Kyushu University, Prof II. Ishii, Chiba University, Dr. S. Naruto, Research Laboratories, Dainiuuon Pharmaceutical Co., Ltd. for kind supply of &mples.*ihanks are also due to the members of Central Analytical Laboratory of this University for NMR and MS measurements.
REFBXRENCE§ 1. Kojima, K. and Anda Y. (1951) f. Pkurm. Sot. Jup. 71, 625. 2. Nonaka, G. and Nishioka. 1. (197.5) Chem Pharm. Buk
23,284:
3. Furuya, T., Ikuta, A. and Syono, K. (1972) Phytochemistry 11, 304j. 4. Haisova, K., Slav& I. and Dolejs, It. (1973) C&l. Czech. Chem. Commun. 38, 3312. 5. Edwards,‘0 E. and flanda, K. L. (l%l) Can. .I. Chem, 39, rsot. 6. Seine, T. 0. and Willette, R. E. (1960) J. Am. Pharm. Assoc. 49, 368. 7. Ikuta, A., Syono, K. and Furuya, T. (1974) Phyt~rn~s~y
13, 2175.
1974 Vol. 15, pp 578-579. Pergamon
Press Prloted zn England
ALKALOIDS AND COUMARINS FROM ZANTHOX YLUM FLA VUM : DIHY~ROR~AECARF~E. A NOVEL P-INDOLOQUINAZOLINE ALKALOID* PETERG. WATERMAN. Department of Pharmaceutical
Chemistry, University of Strathclyde, Glasgow Gl IXW, Scotland (Receiwd 26 September 1975)
Key Wotd Mex-Zanthux~turn thin-bone; ~~ophenanthrid~e;
&rum; Rutaceae; alkaloids; fl~indoloquinuolinr. dihydrorutse~arpmc. canchelery~rine; nitidine; fur~~~~um~rln. imper;ltorrn. ~hzm,xaxanom~.
Pl~plr. Zu~t~xyi~ ~#~ Vahl. (syn. Fwum $auu Krug. et Urb.) Cl]. Voucher. Jimenez 5980 has been de
posited at the herbarium of the Royal Botanic Garden, Edinburgh. Source. Hill sides above La Cue&a, Santiago
519
Short Reports
Province, Dominican Republic. Uses. The wood, known commercially as Jamaican Satinwood, is a timber of high quality [2]. Previous work. The coumarins xanthotoxin, psoralen and suberosin [3] and uncharacterised alkaloids [4] from the wood. PIant parts examined. Root and stem barks. Present work. Soxhlet extraction of the stem bark (200g) with petrol @O-6@), concn of the extract and column chromatography ever Al,O,, eluting with EtOAc, gave imperatorin (75mg) mp 101” (lit. [S] 102-103”). Found M+ 270.0899, C1&11404 requires 270.0892. UV, IR, MS, PMR, were all in close agreement with published data [5-73. No other compounds were isolated from petrol or MeOH extracts of the stem bark but traces of alkaloid were detected. The root bark (1OOg) was similarly extracted with petrol, then CHC&, then MeOH. On shaking with 1N HCl the concn. petrol extract gave a yellow ppt. of chelerythrine chloride (14 mg) mp 200”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Badcation of the acid layer with NI&OH and reextraction into CH,Cl, gave canthin&one (6mg) mp 165”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Similar treatment of the CHCIJ extract gave, on addition of HCl, a yellow-green ppt. of nitidine chloride (46mg) mp 220”, identical in all respects (UV, IR, TLC, mmp) with an authentic sample. Re-examination of the original petrol extract from the root bark revealed the presence of a further alkaloid which was purified by column chromatography over Si gel, eluting with CHCl,, to give white needles (13 mg) mp 168”. [a]$’ -21 (CHCl,; c 0.1). Found M+ 289.1218, C,,H,,N,O requires 289.1215. UV lgAzWnm (log E): 275(3.89), 292(3.76), 304sla(3.45), 31q3.24). IR v,,, (KCl) cn- ‘: 3350-3320 (NH), 1680 (CO), 1610, 1470, 1375. PMR @MHz, CDQ): 6 3.28 (2H, t, J 7Hz, CH,-14), 4.30 @I-I, t, J 7Hz, C&-15), 690 (lH, d, J 2Hz, H-6), 7.3g8.60 (8H, m, 8 x H-Ar), >lOOO (2H, both replaceable by DzO, 2 x N-H). MS: m/e 289(14%), 288(2), 287(06), 170(0.4), 169(1.0), 159(1.5), 147(3.3), 146(1.4), 143(100), 142(8.3), 130(33), 119(@4), 115(5.6). The occurrence of 3 x N in the molecule suggested the alkaloid was of the rare fl-indoloquinazoline class IUIOWII only from the Rutaceae [8]. This assumption was sustained by examination of IR (CO and NH) and MS. The complex fragmentation pattern of the latter can be rational&d by postulating fission of the b-indoloquinazoline nucleus between C6-N, and C12-N13 or between C,;C, and either N,&, or C14-C1s. The occurrence of the indolic fragments at m/e 143 and m/e 130 as major ions is in accord with findings for similar compounds [9,10]. The PMR confirmed both the presence of the 3 C-CH,-CHIN< moiety[l l] and the lack of any substitution on the molecule. The combined spectral data thus suggested that this was a novel member of the 8indoloquinazoline class of alkaloids in which the empirical formula C,sH,,NJO had been previously unknown. From the lack of substituents, presence of 2 x NH, optical activity and UV, in which 1,,is in close agreement with evodiamine (l), it seems that this new alkaloid must be dihydrorutaecarpine (2).
* Part 7 in the series “Chemosystematics For Part 6 see ref. [S].
in the Rutaceae”.
( 1) R = Me
(2) R = H
Direct evidence for structure (2) was obtained by reduction with LiAlH4 in dry Et,0 [1x13]. Refluxing for 10 hr gave, on recrystallisation from EtOH, indolo-[2’,3’ :3,4]-pyrido-2, lb-quinazoline, mp 162” (lit. [12] 161-163”), identical in all respects (UV, IR, mmp) with material obtained on reduction of rutaecarpine by the same method. Further evidence for structure (2) was obtained from methylation with Me1 in boiling MeOH. A mixture was obtained the major component of which was identical (TLC-3 systems) with evodiamine. Examination of the partially purified MeOH extract of the root bark by methods previously described [14] revealed the presence of small amounts of quaternary alkaloids of which one was tembetarine (TLC, UV). Biological signijcance. Whilst the type and distribution of alkaloids in 2. flauum appears typical of the genus [8,15] the presence of canthin-6-one and dihydrorutaecarpine may have additional systematic significance. Certainly the recent suggestion [16] that a close biochemical relationship exists between Central American and South East Asian species is supported by the isolation of a /?-indoloquinazoline from Z. jautun. Acknowledgemenr~The author wishes to extend his thanks to Dr. J. Jimenez, Calle Maxim0 Gomez 34, Santiago de 10s Caballeros, Dominican Republic, for the collection and identification of plant material and to Dr. R. D. Waigh, Department of Pharmaceutical Chemistry, University of Strathclyde, for PMR spectra. REFERENCES
1. Wilson, P. (1911) North Atnerican Florq Vol. 25, p. 196; Adams, C. D. (1972) Flowering Plants of Jamaica, p. 385, University of the West Indies, Mona, Jamaica. 2. Department of Scientific and Industrial Research, London (19561 Handbook of Hardwoods. D. 209. H.M.S.O. 3. King, J. E., Housliy, J. R. and i